Synthesis of substituted N-phenylmaleimides and use in a Diels–Alder reaction: a green multi-step synthesis for an undergraduate organic chemistry laboratory
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Summary
This paper presents a minimally hazardous, environmentally friendly, and energy-efficient reaction sequence for a sophomore-level Organic Chemistry lab, aimed at synthesizing N-phenylmaleimide precursors for a Diels–Alder reaction. The synthesis, which involves two steps from maleic anhydride and a substituted aniline, produces a valuable class of compounds with biological significance. The experiment emphasizes green chemistry principles such as atom economy, safer chemicals, energy efficiency, waste reduction, and accident prevention. Students also use 1H NMR spectroscopy to characterize the products.
Full Citation
Bastin, L. D., Nigam, M., Martinus, S., Maloney, J. E., Benyack, L. L., & Gainer, B. (2019). Synthesis of substituted N-phenylmaleimides and use in a Diels–Alder reaction: a green multi-step synthesis for an undergraduate organic chemistry laboratory. Green Chemistry Letters and Reviews, 12(2), 127–135. https://doi.org/10.1080/17518253.2019.1609596
Full Citation
Bastin, L. D., Nigam, M., Martinus, S., Maloney, J. E., Benyack, L. L., & Gainer, B. (2019). Synthesis of substituted N-phenylmaleimides and use in a Diels–Alder reaction: a green multi-step synthesis for an undergraduate organic chemistry laboratory. Green Chemistry Letters and Reviews, 12(2), 127–135. https://doi.org/10.1080/17518253.2019.1609596
Safety Precautions, Hazards, and Risk Assessment
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